Cyanoacetic acid → 2-Cyano-N-(2-methyl-6-nitrophenyl)acetamide

HRID 1364300Notes

Reaction equation

HRID 1364300 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:3]=1[NH2:4].[C:12]([CH2:14][C:15](O)=[O:16])#[N:13].P(Cl)(Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[C:12]([CH2:14][C:15]([NH:4][C:3]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1])=[O:16])#[N:13]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 112982-Methyl-6-nitroanilineHCID 24819Phosphorus pentachloride

Product 1

HCID 215049312-Cyano-N-(2-methyl-6-nitrophenyl)acetamideYield 66.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-methyl-6-nitroaniline (25 g, 164.3 mmol) in benzene (200 mL) were added cyanoacetic acid (14.5 g, 170.46 mmol) and PCl5 (35 g, 168 mmol). The reaction mixture was heated at 60° C. for 7 h. After cooling to rt, the reaction mixture was filtered and the solid was washed with benzene and water. The solid was dried under reduced pressure to afford the title acetamide (24 g, 109 mmol) as a yellow solid.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationthe reaction mixture was filtered
  3. washthe solid was washed with benzene and water
  4. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-a5da6707aa424878a787301357002749
Source dataset
uspto-grants-2011_02
Patent number
US07888359B2

Reaction notes

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